Reader request: What to wear when you don't know what to wear
a step by step guide + inspo & links
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links and prices updated 8/31/25
New feature everyone! Paid subscribers will get to submit styling questions and requests. Do you have a recent purchase that you don’t know how to style, or an upcoming event and you’re stuck on what to wear? Are you on TRR or eBay hunting for something specific and feeling overwhelmed, and want a curated, custom list? (you’ll also get early access to the post you request!) Consider becoming a paid subscriber and DM me!
This request comes from Elizabeth, who in addition to being my oldest friend (and, more importantly, a paid subscriber), is someone who always looks fab and who I know to have good taste. However, as a mom she’s struggling with a specific styling problem that is *not* specific to moms. It’s all about wtf do you wear for life’s mundane, daily tasks (like grocery shopping or, in her case, school drop-offs) when you’re tired, but also tired of looking schlubby (then keep scrolling for inspo + shopping recs):
“I’d love your take on styling for “cool mom at drop-off”! Something that feels effortless and pulled together, but realistic for someone juggling 2 toddlers, a demanding job, and negative time. I’m after something easy and comfortable but that still feels like ME - artsy, fun, and a little elevated but doesn’t take much to pull off”
Right off the bat, two things:
Relatable. I can unequivocally say that since becoming a mom last year, the quality of my outfits has suffered immensely. I would describe my day-to-day style as “the path of least resistance”. Putting together a cute outfit takes mental clarity and energy that I simply do not have, and wearing fun things that used to bring me joy - like Manolo Blahnik mules or a mini dress, say - is completely impractical now. This makes me sad, but so much of motherhood is about trying to claw back the person you used to be, while also learning to celebrate the person you are now.
“Cool” and “effortless” may be two of the most triggering words in the English language. They’re incredibly rarified qualities you can’t fake or manufacture, but the fashion industry and social media keep telling us we must be cool and effortless at all times in order to achieve some form of self-actualization. My first piece of advice for anyone reading is to simply ban those words and their implications from your brain - you will generally be a lot more content in life.
This request seems simple on it’s face but it’s not. What you wear to drop-off generally isn’t important - it’s not exactly your wedding - but it is a daily, low-stakes exercise in presenting yourself to your peers (peers that, at minimum, you want to have friendly relationships with). In a way, because it is a banal, everyday task, it feels like it is more representative of you and your style then something like going on vacation, where you pack the crème de la crème of your wardrobe. It’s the type of situation where just throwing on sweats would be perfectly fine and socially acceptable, but also one that - like Elizabeth - not feeling like your best self every day starts to wear you down.
This is the part of the post where I opt to take the more complicated but sincere route to answer her request, because she is my dear friend (and paid subscriber) and I want to put the “personal” into personal styling. It would be much simpler to just post a bunch of links to trendy shit that she might like for a week, but that wouldn’t address the fundamental problem she’s having. Anyone with money to spend can have a closet full of “cool” clothes, but I think she’s after something deeper. She wants to feel cool in her clothes, to reach the nirvana of having so much confidence and conviction in your clothing choices you actually stop caring what people think - in other words, true effortlessness. Here’s my advice to anyone feeling stuck in a similar way:
If you’re not sure how to define your personal style, here’s the secret: it’s simply an amalgamation of the things you like and that speak to you. That’s it. If you like everything Alexa Chung wears but dress nothing like her because you don’t have the means to (but would if you could!), then bingo - your style is like Alexa Chung’s (congratulations). What you wish you were wearing is more indicative of your taste than that old t-shirt you’re actually wearing because your toddler might throw up on it.
Your personal style IS your taste, and it’s essential that you know it and trust it, because you CANNOT be well dressed without confidence in your taste. Look at any “cool” mom on IG or in the smoothie line at Erewhon and repeat after me: 👏🏼 it’s not the clothes that make them cool, it’s the confidence that they have in their clothes 👏🏼
Visuals are extremely helpful: screenshot everything that speaks to you and every outfit you’ve worn that you feel good in and put it in albums you can reference when your brain feels mushier than the puree your baby just threw on the floor.
Cancel date night this week (sorry Matt) and have a date with your clothes instead - try everything on, and be honest and realistic in how you feel in it (anything that doesn’t feel right or fit, get rid of. I hear The RealReal is looking). Putting outfits together uses a muscle in your brain that will atrophy if you don’t flex it every now and then. This is an exercise in self reflection, literally, it’ll help reveal what you want to see in your own reflection, and will provide clarity as to what your wardrobe building blocks are. You only have to do this once every few years and it will save you so much time in the future.
Drop-off clothes by definition need to be so easy and authentic to us that we can just throw them on without a second thought while kids and partners and dogs all vie for our attention. Identifying those pieces is the first step. The second step is figuring out how to add that magic it quality - what she’s calling cool, effortless, artsy, and elevated - then the third step is adding a sprinkle sprinkle of extra intrigue. Using these, you’re going to build a variety of outfit formulas that you simply have to follow in the morning, varying and modifying each day - here’s how I break it down:
As mentioned, start with building blocks. This is not the same as “basics” or “capsule wardrobe” (other triggering words), this is simply the bread and butter items in your closet you reach for first when getting dressed in a crunch. I call them building blocks because they’re the foundation that you build the rest of your outfit on. My personal examples: stretchy pants, cotton shorts, cropped trench jacket, denim button up, crewneck sweaters, graphic tees, gold mesh flats and loafers
Once you have a sense of those, your next task is to identify which pieces are the it pieces, the ones that are a little more complicated and interesting, the ones that you are itching to wear but pass over in the morning because you don’t have time/brain capacity to style. My personal examples: cute pj/lounge sets, any sort of dress or skirt, any form of intentional layering, any non-stretchy pants and shoes I can’t just slip on, prints/bright colors
Next - your sprinkle pieces: basically accessories, but anything that adds an extra oomph - makeup counts! My personal examples: hats, jewelry, a watch, sunglasses, a fun bag, lipstick and mascara
Lastly, mix and match all of the above and take photos of the results you like. For example, an it piece of mine is this pajama/lounge set I can’t wear alone without feeling too naked or like I literally just rolled out of bed (I did). Throwing on a more structured, building block piece like my cropped trench takes care of that, and then black loafers make it feel more elevated. Lastly, gold jewelry, black sunglasses, and a baseball cap turn it into an *outfit*. Once I have that, it’s just a matter of switching up each formula every day - maybe instead of the pajama set, the next day it’s the same trench jacket but with jeans and a tee instead.
Et voilà! Keep scrolling for my picks for ideal drop-off/Trader Joe’s run/dog park fits:
Clockwise-ish L to R: SOLD Lafayette 148 jacket, $60 with no markdown yet
Ralph Lauren baseball cap, $59 brand new
SOLD Seiko watch, $62 - if you’re in the market for one, Seiko is a solid option for affordable quality vintage watches
Handmade twisted pearl necklace, $61 - I just got a similar vintage necklace and can confirm it’s an outfit maker + here's a cheaper one
Marni jumpsuit, $60 at 25% off - one and done baby!
SOLD Prada patent loafers, $82 at 65% off
Selkie graphic sweatshirt, $80 at 30% off
SOLD Staud mini shorts, $30 at 40% off
SOLD Akris x Bergdorf Goodman trench coat, $68 at 20% off - this one and this one are good
Ralph Lauren two-tone loafers, $87 at 30% off - love these too
Vince knit set, $87 at 35% off
Chloé Shearling Slides, $92 at 50% off - looks very lightly worn which is essential for buying shearling second hand
Clockwise-ish L to R: SOLD Kenzo graphic half-zip, $64 at 20% off
SOLD Velvet Canyon black sunglasses, $75 at 40% off
Seiko watch, $55
SOLD Vintage - Unbranded fur hat, $43 at 65% off
SOLD Clare V. graphic t-shirt, $82 at 50% off
Celine drawstring pants, $94 at 35% off
SOLD Jimmy Choo mesh ballet flats, $52 at 20% off - marked “fair” but the exterior looks good
SOLD House of Harlow knit set, $80 at 30% off
SOLD Gucci flats, $97 at 25% off
London Fog stand collar jacket, $20 at 50% off - I like this one too
SOLD Claudie Pierot knit pants, $81 at 40% off - marked as a set, may or may not be. Order and find out!
SOLD Alexander McQueen graphic tee, $69 at 40% off
SOLD Prada patent leather loafers, $116 at 20% off - another pair here, similar but cheaper
Bally loafers, $47 at 50% off - another really good pair
Bill Blass silk sweatpants, $60 with no markdown yet - Karl Lagerfeld once called sweatpants a sign of defeat, imo silk ones should be exempt
Clockwise-ish L to R: SOLD Needles mohair cardigan, $100 at 20% off
SOLD Anna Sui bucket hat, $87 at 40% off - a fun alt
Beaded necklace, $28
SOLD Yves Saint Laurent sunglasses, $99 at 40% off
SOLD COS denim shacket, $47 at 50% off
LSpace knit drawstring pants, $29 at 65% off
Salvator Ferragamo patent loafers, $57 at 50% off
SOLD Alice + Olivia drawstring shorts, $44 at 20% off
SOLD Sea New York quilted jacket, $78 at 55% off - she's good too
SOLD Acne Studios graphic t-shirt, $99 at 5% off
SOLD The Row satin loafers, $93 at 70% off
Wales Bonner x Adidas sneakers, $87 at 55% off
SOLD Danielle Guizio knit drawstring pants, $38 at 30% off
Wales Bonner x Adidas sneakers, $117 at 40% off - these too!
SOLD Tory Burch sweatpants, $44 at 20% off - I have these in green and they are one of my most worn items in the fall and winter
Clockwise-ish L to R: SOLD REMAIN Bergin Christensen set, $97 at 50% off
Barney's New York leather bucket hat, $51 at 55% off
Velvet Canyon tinted sunglasses, $54 at 40% off
SOLD Vintage herringbone necklace, $48
SOLD Tory Burch cropped jacket, $76 at 20% off
Marni knit drawstring pants, $48 at 40% off
SOLD Onitsuka Tiger sneakers, $116 at 20% off
Salvatore Ferragamo graphic t-shirt, $63 at 40% off
Simon Miller shorts, $35 at 30% off
SOLD Ralph Lauren denim shirt, $45 - hard to top the classic, here's another
Fifi Venezia friulane slippers, $55 at 70% off - Friulane slippers are a great errand shoe - here's an Etsy shop that makes them
SOLD London Fog utility jacket, $17 at 50% off
SOLD Kate Spade gold flats, $30 at 40% off
And remember - you’re doing amazing sweetie. Thanks for reading!
Xx Karina 🦐
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You are a godsend! It’s been 24 hours and I’ve already returned to this post multiple times - and know I will again and again! Next problem to help solve for me: my upcoming amex bill
So good! Love to see what a motherfucking SME you are about this. It’s cliche but following your joy is key. Also, shifting the focus to only buying shit you LOVE has served me. An annoying aside from elderly, once divorced me, don’t cancel date night. Nurturing the relationship w ur partner’s the priority. School moms you want to be seen by come and mostly go. I could wax poetic about how fleeting this time in a young mom’s life is but I’ll spare you. Thanks for these posted gems.